Patent GB-191109111-A (GB)
Title: Manufacture and Production of Anthraquinone Derivatives.
Inventor: NEWTON PHILIP ARTHUR
Filed: 1911-04-12
Granted: 1912-03-28
Abstract: 9111. Newton, P. A., [Farbenfabriken vorm. F. Bayer & Co.]. April 12. Anthraquinoneiminazoles, which are dyes or parent materials for dyes, are obtained:-(1) by heating monoacyl-o-diaminoanthraquinones or derivatives thereof with or without diluents or dehydrating-agents; (2) by heating diacyl-odiaminoanthraquinones with acid-eliminating agents; (3) by heating o-diaminoanthraquinones or derivatives thereof with acylizing-agents until the iminazole ring is formed; (4) by condensing o-diaminoanthraquinones or derivatives thereof with aldehydes of the aliphatic or benzene series, oxidation being effected at the same time. The following products are specified: - 1: 2 - phenylanthriminazole, which dyes yellow shades from a vat, by heating monobenzoyl-1:2-diaminoanthraquinone with sulphuric acid, or by heating 1:2-diaminoanthraquinone with benzoyl chloride or with benzaldehyde ; 4-amino-1:2-phenylanthriminazole, which dyes greenish-blue-grey shades from a vat, by heating benzoyl - 1:2:4 - triaminoanthraquinone with sulphuric acid, or by heating 1: 2 : 4 - triaminoanthraquinone with benzaldehyde in nitrobenzene; the acyl derivatives of this compound are also vat dyes, for example, the benzoyl derivative dyes orange shades; an aminoanthriminazole, dyeing greenish - blue shades from a vat, from 1:2:4-triaminoanthraquinone and o-chlorbenzoyl chloride; the benzoyl derivative of this compound dyes orange shades from a vat; oxy-1:2-anthriminazole by heating 1: 2-diaminoanthraquinone with phosgene in nitrobenzene; 2:3-anthriminazole by heating 2:3-diaminoanthraquinone with formic acid; an iminazole of the formula by heating dinitro - 2 - aminoanthraquinone urethane (Specification 12,756/05) with ptoluidine; the sulphonic acid of this compound dyes wool yellow shades; 1: 2-methylanthriminazole by treating 1:2-diaminoanthraquinone with p - acetaldehyde in sulphuric acid; 4 - ptoluido-1:2-phenylanthriminazole, which dyes green shades from a vat, by heating 1:2-diamino-4-p-toluidoanthraquinone with benzaldehyde in nitrobenzene; the sulphonic acid of this compound dyes wool blue; an iminazole is obtained by heating 1-p-toluido-2-amino-3-bromanthraquinone with benzaldehyde in nitrobenzene. Specification 24,429/06 is also referred to. Anthraquinoneoxazoles are obtained by condensing o-aminooxyanthraquinones with aldehydes of the aliphatic or benzene series; 4- amino - 1:2 - phenylanthraquinoneoxazole, obtained from 1-oxy-2:4-diaminoanthraquinone and benzaldehyde dyes red shades turning to yellow from a vat; its benzoyl compound dyes yellow shades from a vat. Anthraquinonethiazoles are obtained by cor.- densing o-aminomercaptoanthraquinones with aldehydes of the aliphatic or benzene series; phenyl-1:2-anthrathiazole is obtained from 1- aminoanthraquinone-2-mercaptan and benzaldehyde; 4-p-tolylamino-1:2-phenylanthrathiazole, from 1-amino-4-p-tolylaminoanthraquinone-2-mercaptan and benzaldehyde, yields on sulphonation a violet wool dye; 3-brom-1:2- phenylanthrathiazole, from 2-amino-3-bromanthraquinone-1-mercaptan and benzaldehyde, is a yellow vat dye; 1-p-tolylamino-2:3-phenylanthrathiazole, from 1-p-tolylamino-2-aminoanthraquinone-3-mercaptan and benzaldehyde, is a violet-brown dye; its sulphonic acid dyes wool bluish-red. Benzoylaminoanthraquinones - Monobenzoyl- 1:2-diaminoanthraquinone and mono-, di-, or tri - benzoyl-1:2:4-triaminoanthraquinone are obtained by treating 1:2-di- or 1:2:4-triaminoanthraquinone respectively with benzoyl chloride in nitrobenzene solution.